This achievement is for dying 86 times. If you want to get this achievement the quickest, choose the character "The Drifter" as that one starts with the least amount of health. Although the game is a rougelike and different each run, the beginning tutorial area is the same every time which means you can run forward just a bit until you see a spike trap on the ground. You can't miss it as it is directly in your path. Simply stand in it until it kills you. The achievement will pop when you die a total of 86 times.